It has long been assumed that homelessness is a personal choice. As a choice, homelessness is embedded within debates about deviant behaviours and problematic pathologies. The “homeless person” is either making calculated and immoral choices to be homeless, or they are perceived to be powerless agents who lack the capacity to exercise choices. Rarely has it been adequately explained, however, what choosing homelessness means and how people who are homeless make sense of their choices. The structural and individual circumstances that situate and make choices meaningful require robust consideration. Drawing on ethnographic research with people sleeping rough, this article unpacks and illuminates some of the hidden complexities that underpin choices to be homeless. With an objective of retaining people’s sense for autonomy, the article contributes to the field by arguing that choice can be understood as an expression of agency and a commitment to a “normal” identity.